Southeast Wisconsin Holidays from NZ$2,826

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The Latest Southeast Wisconsin Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
Price was NZ$3,315, price is now NZ$2,826 per person
NZ$2,826
per person
13 Aug - 18 Aug
found 19 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,248 reviews)
Requested a room with a walk in shower as I have a broken foot and am wearing a walking boot. Was told none were available but online through the hotels own website it showed they were and were bookable for my entire stay. Rude front desk staff. Probably will never stay there again. This hotel has gone down hill for sure

Reviewed on 25 May 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was NZ$4,055, price is now NZ$3,237 per person
NZ$3,237
per person
12 Aug - 17 Aug
found 19 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (2,310 reviews)
Very convenient to airport for late arrival after overseas flight and for early departure without need for train or cab etc. would recommend highly for this reason and will use again. Room was clean, cool, and quiet.

Reviewed on 26 May 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was NZ$4,302, price is now NZ$3,509 per person
NZ$3,509
per person
12 Aug - 17 Aug
found 19 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
The room was clean and the staff were very nice and helpful. My only complaint is that the hotel is clearly dated and worn. They are undergoing a renovation, but our room was one of the older ones. The room was still fine, but the sink water pressure was very low. They did offer to have an engineer look at, but since our stay was so short we didn't bother with it.

Reviewed on 18 May 2026

Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
Price was NZ$3,674, price is now NZ$3,097 per person
NZ$3,097
per person
12 Aug - 17 Aug
found 19 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,388 reviews)
Clean bed and bathroom; comfortable bed; sofa and other furniture is old; staff friendly; daily housekeeping; breakfast is average; live omlette station is pouplar; Hotel is 10-15min walk from Rosemont station; fashion outlets of Chicago is also about 10-12 min walk from the hotel; hence location is convenient;

Reviewed on 26 May 2026

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
Price was NZ$3,349, price is now NZ$2,834 per person
NZ$2,834
per person
12 Aug - 17 Aug
found 19 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,843 reviews)
Very friendly staff, room was super clean and lots of nearby restaurants and 5 minutes from airport. Great location!

Reviewed on 29 May 2026

Our guide on where to stay in Southeast Wisconsin

Find the best Southeast Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southeast Wisconsin
Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Southeast Wisconsin Holiday

Our pick of the best Southeast Wisconsin Hotel Deals

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is NZ$295 per night from 2 June to 3 June
NZ$295
2 June - 3 June
includes taxes & fees
9.2/10 Wonderful! (1,500 reviews)
"The property was nice but the shuttle bus to the Brewers game was delayed by an hour for the ride back to the casino because of staffing issues so 30 of us were not very happy but the overall stay was good"

Reviewed on 28 May 2026

Potawatomi Hotel & Casino
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
The price is NZ$439 per night from 14 June to 15 June
NZ$439
14 June - 15 June
includes taxes & fees
9.6/10 Exceptional! (2,112 reviews)
"The Pfister Hotel is a lovely place to stay at. It's breathtaking, the food was delicious, very clean, and the staff was fabulous. We enjoyed our time at the lobby enjoying a drink and the music provided by the piano player. I highly recommend The Pfister when visiting Milwaukee/"

Reviewed on 29 May 2026

The Pfister Hotel
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is NZ$294 per night from 31 May to 1 June
NZ$294
31 May - 1 June
includes taxes & fees
9.2/10 Wonderful! (1,346 reviews)
"A"

Reviewed on 28 May 2026

Harbor Shores on Lake Geneva
See all 2,424 properties in Southeast Wisconsin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Southeast Wisconsin

Milwaukee County Zoo

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo
Henry W. Maier Festival Park

Henry W. Maier Festival Park

Enjoy an outing to Henry W. Maier Festival Park during your stay in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Henry W. Maier Festival Park
Buildings along the Milwaukee River at night, in Milwaukee, Wisconsin.

Milwaukee River Walk

After visiting Milwaukee River Walk, make a plan to see the other sights and activities in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Milwaukee River Walk

Frequently asked questions

Can I cancel my flight booking to Southeast Wisconsin due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel queries, including about flight changes related to COVID-19. For more peace of mind, read through the terms and conditions of your preferred airline before reserving your tickets.
What's the best way to find cheap flights to Southeast Wisconsin that have flexible change policies?
We know that things can change in the blink of an eye, so locking in a flexible airfare with Expedia makes good sense. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-priced, flexible flight to Southeast Wisconsin is just a few clicks away.
What are some of the general tips for travellers to Southeast Wisconsin during the COVID-19 outbreak?
With strict COVID-19 precautions in effect, travel looks a lot different today. Here's what you need to know before you pack your suitcase for Southeast Wisconsin:
  • Find out if any travel restrictions apply to your destination and origin before booking anything. Also check if there are any special conditions you'll have to follow on arrival, such as proof of a negative COVID-19 test.
  • Wear a face mask even during airport screening. A TSA officer will ask you to lower your mask temporarily for identification purposes.
  • Instead of handing a TSA employee your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection.
  • You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. You'll need to remove it for X-ray screening.
  • Remove items from your pocket, like your phone, keys and wallet, and place them in your carry-on rather than into bins. This will minimize handling during screening.
  • If you want to take food on board, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA agent will need to touch your food container or carry-on bag for inspection.

Which airlines fly to Southeast Wisconsin?
Delta is a major carrier servicing Southeast Wisconsin. Book an airfare to General Mitchell Intl. Airport (MKE) and you'll have 573 Delta flights each month to select from.
How can I find cheap tickets to Southeast Wisconsin?
One of the easiest ways to snare cheap tickets to Southeast Wisconsin is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. You'll see the cheapest prices for nearby days. The best price for a flight to Southeast Wisconsin in the last seven days was . Booking well ahead will usually help you walk away with an even bigger bargain.
How much is a flight to Southeast Wisconsin?
One-way flights leaving () sold for as little as in the last seven days. During this period, the cost of a return airfare to Southeast Wisconsin ranged between and . If you spot a deal, book quickly — these prices don't hang about.
What are the most popular airports to fly into in Southeast Wisconsin?
General Mitchell Intl. Airport (MKE) is the main entrance point for those hoping to explore Southeast Wisconsin. Approximately 2400 flights a month touch down here.
When is the cheapest time to fly to Southeast Wisconsin?
If you can be flexible with your travel dates to Southeast Wisconsin, try to leave early in the week. The cheapest day to take off is usually Tuesday, followed by Monday. Saturday is typically the most expensive day, with a lot of people preferring to take off on the weekend.
How much is a plane ticket to Southeast Wisconsin?
Ticket prices ranged from to over the last seven days. When you're ready to book, we'll help you lock in the best price to Southeast Wisconsin.
Which airlines with flights to Southeast Wisconsin employ COVID-19 cleanliness policies?
While flying during a pandemic can be slightly overwhelming, airlines have gone above and beyond to protect the well-being of passengers and crew. These are a few carriers that have implemented changes:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.